Question 1

How far in advance should I book a flight to Chicago?

Accepted Answer

You are more likely to see cheaper flights to Chicago from Toronto when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 396 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as C$ 270 on momondo.

Question 2

How have Toronto to Chicago flight prices changed over time?

Accepted Answer

As of January 2026, prices for Toronto to Chicago flights are approximately 18% cheaper when compared to flights at the same time last year.

Question 3

What is the cheapest Toronto to Chicago flight route?

Accepted Answer

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices

Question 4

What is the cheapest airline that flies from Toronto to Chicago?

Accepted Answer

United Airlines, Porter Airlines, and Air Canada are the most popular carriers operating from Toronto to Chicago

Question 5

What day of the week experiences the fewest flight delays on this route?

Accepted Answer

Tuesday is statistically the day of the week that experiences the fewest delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

Question 6

What is the cheapest month to fly to Chicago?

Accepted Answer

The month of June is another great option to travel to Chicago, with average flight prices from Toronto averaging around C$ 311.

Question 7

Which airlines fly to Chicago?

Accepted Answer

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Toronto according to our data. Air Canada is the first choice among our users, with 60% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Question 8

How often are flights from Toronto to Chicago delayed?

Accepted Answer

Historically, on average around 11% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 139 minutes.

Question 9

What is the most punctual flight time for Toronto to Chicago flights?

Accepted Answer

Generally, flights departing at night tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

Question 10

How many flights depart from Toronto to Chicago on average per week?

Accepted Answer

369 flights are operational weekly from Toronto to Chicago as of January 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

Question 11

Which airline has the best punctuality record on Toronto to Chicago flights?

Accepted Answer

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 6% of their flights experiencing any sort of delay.

Question 12

What cabin class options are available on Toronto to Chicago flights?

Accepted Answer

There are 4 cabin classes available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Question 13

Can stopping save me money on Toronto to Chicago flights?

Accepted Answer

No. A direct flight is the cheapest option for a flight between Toronto to Chicago.

Question 14

How long does it take to fly to Chicago?

Accepted Answer

Flight times from Toronto to Chicago vary, but if you’re flying out of Toronto and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 5h 11m on average. Another popular route from Toronto to Chicago is flying from Hamilton to Chicago O'Hare Intl Airport, which will take roughly 11h 46m. Keep in mind that layovers or delays could extend your travel time.

Question 15

What is the typical price of a round-trip flight between Toronto and Chicago?

Accepted Answer

Prices are currently low for flights on this route.Typical prices usually range from C$ 317 to C$ 529.
The lowest price recently found on this route was C$ 254.

Question 16

What is the cheapest time of day to depart on your flight to Chicago?

Accepted Answer

In the evening is the cheapest time of day to fly from Toronto to Chicago when you can find flight prices for as low as C$ 635. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,083 per ticket.

Question 17

How many flights depart from Toronto to Chicago on average per day?

Accepted Answer

52 flights are operational daily from Toronto to Chicago as of January 2026. The most popular departure time for this route is 6:00a.m., with 49% of flights per day taking off at noon.

Question 18

What is the cheapest day to depart on your flight to Chicago?

Accepted Answer

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 584. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,040. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

Question 19

What are the airports for flights from Toronto to Chicago?

Accepted Answer

If you are making a trip from to Chicago from Toronto, you will find that there are two airports in the Toronto area that offer flights to Chicago. They include Toronto Island Airport (YTZ) and Toronto Pearson International Airport (YYZ). Two airports are available in the Chicago area: Chicago O'Hare International Airport (ORD) and Chicago Midway Airport (MDW). Toronto Pearson International Airport Chicago O’Hare International Airport are the larger and busier airport options in their respective cities.

Question 20

Which airlines offer direct flights from Toronto to Chicago?

Accepted Answer

There are several options for nonstop flights between Toronto and Chicago. Porter Airlines offers a nonstop flight that travels between Toronto Island Airport and Chicago Midway Airport. Air Canada operates a nonstop flight that travels between Toronto Pearson International Airport and Chicago O'Hare International Airport. In addition, both United Airlines and American Airlines operate nonstop flights along this same route from Toronto Pearson International Airport to Chicago O'Hare International Airport.

Question 21

What are the best places to stop between Toronto and Chicago?

Accepted Answer

Beyond the very convenient nonstop flights offered between these two cities, you will also find some one-stop flight options available that can save you money on your trip from Toronto to Chicago. Air Canada offers a one-stop flight with service from Toronto Island Airport to Chicago O'Hare International Airport with a layover at Montreal Pierre Elliott Trudeau International Airport (YUL) that will add about four hours to your travel time compared to the nonstop options. Air Canada also offers a one-stop flight from Toronto Pearson International Airport to Chicago O’Hare International Airport that will also add about four hours to your travel time. Delta Airlines provides a one-stop flight from Toronto Pearson International Airport to Chicago O' Hare International Airport with a layover at New York LaGuardia Airport (LGA). You will also find a one-stop flight operated by United Airlines between Toronto Pearson International Airport and Chicago O'Hare International Airport with a layover at Cleveland Hopkins International Airport (CLE).

Question 22

Do you need a visa or a passport to fly from Toronto to Chicago?

Accepted Answer

As a Canadian citizen traveling to the United States, you will need to provide proof of Canadian citizenship upon entry into the United States. You can do this by presenting a passport, which must be valid for the entire duration of your stay. Alternatively, you can use a valid NEXUS card, which you can use at a self-service kiosk at the airport in Chicago. Most Canadian visitors will not need a visa to travel to the United States for a stay of up to six months. When you arrive in the US, you are required to declare the intended duration of your stay in the country.

Question 23

When did momondo last update prices for flights from Toronto to Chicago?

Accepted Answer

Prices for flights from Toronto to Chicago are updated daily.

Question 24

How many operators does momondo search for flights from Toronto to Chicago?

Accepted Answer

There are 5 operators available for flights from Toronto to Chicago as of January 2026.

Question 25

How old do you have to be to fly from Toronto to Chicago?

Accepted Answer

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto to Chicago.

Question 26

What documentation or ID do you need to fly to Chicago?

Accepted Answer

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best price found	C$ 198
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	3 airports

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 196	Free Cancellation	Rating 8.0 406 reviews	Search Porter Airlines flights
Air Canada	PriceFrom C$ 257	Free Cancellation	Rating 7.1 10,603 reviews	Search Air Canada flights
American Airlines	PriceFrom C$ 260	Free Cancellation	Rating 7.2 11,097 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 263	Free Cancellation	Rating 7.4 9,143 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 369	Free Cancellation	Rating 7.2 3,235 reviews	Search WestJet flights

Cheap flights from Toronto to Chicago from C$ 158

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 5/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from Toronto to Chicago

What is the typical price of a round-trip flight between Toronto and Chicago?

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Toronto averaging around C$ 311.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Toronto to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Toronto to Chicago flights?

There are 4 cabin classes available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto to Chicago flights?

No. A direct flight is the cheapest option for a flight between Toronto to Chicago.

How have Toronto to Chicago flight prices changed over time?

As of January 2026, prices for Toronto to Chicago flights are approximately 18% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Toronto to Chicago?

United Airlines, Porter Airlines, and Air Canada are the most popular carriers operating from Toronto to Chicago

Which airlines fly to Chicago?

How often are flights from Toronto to Chicago delayed?

Historically, on average around 11% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 139 minutes.

What is the most punctual flight time for Toronto to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week that experiences the fewest delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 6% of their flights experiencing any sort of delay.

How many flights depart from Toronto to Chicago on average per day?

52 flights are operational daily from Toronto to Chicago as of January 2026. The most popular departure time for this route is 6:00a.m., with 49% of flights per day taking off at noon.

How many flights depart from Toronto to Chicago on average per week?

369 flights are operational weekly from Toronto to Chicago as of January 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

How long does it take to fly to Chicago?

When to book flights from Toronto to Chicago

Cheap Toronto to Chicago (YTO to CHI) flight deals and tips

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When did momondo last update prices for flights from Toronto to Chicago?

How many operators does momondo search for flights from Toronto to Chicago?

How old do you have to be to fly from Toronto to Chicago?

What documentation or ID do you need to fly to Chicago?

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What is the most popular airline from Toronto to Chicago?

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